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1,1'-Sulfonyldiimidazole

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Name

1,1'-Sulfonyldiimidazole

EINECS 230-554-0
CAS No. 7189-69-7 Density 1.6 g/cm3
PSA 78.16000 LogP 0.80160
Solubility N/A Melting Point 135-137 °C(lit.)
Formula C6H6N4O2 Boiling Point 471 °C at 760 mmHg
Molecular Weight 198.205 Flash Point 238.7 °C
Transport Information N/A Appearance light cream crystalline powder
Safety 26-36-36/37/39 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 7189-69-7 (1,1'-Sulfonyldiimidazole) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Imidazole,1,1'-sulfonyldi- (7CI,8CI);1,1'-Sulfonylbis(1H-imidazole);1,1'-Sulphonylbis-1H-imidazole;

Article Data 18

1,1'-Sulfonyldiimidazole Synthetic route

18156-74-6

1-(Trimethylsilyl)imidazole

7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
With sulfuryl dichloride In toluene at -10℃; for 4h;98%
With fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -1 - 26℃; under 35.2535 - 697.57 Torr; for 0.566667h; Temperature; Pressure; Reagent/catalyst; Autoclave; Cooling with ice;92%

1H-imidazole-1-sulfonyl fluoride

18156-74-6

1-(Trimethylsilyl)imidazole

7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 50 - 53℃; Reagent/catalyst; Temperature;97%
288-32-4

1H-imidazole

7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;92%
With sulfuryl dichloride In dichloromethane at 0 - 20℃; for 15h;90%
With sulfuryl dichloride In dichloromethane at 0 - 20℃;90%
288-32-4

1H-imidazole

7791-25-5

sulfuryl dichloride

7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 16h;87%
288-32-4

1H-imidazole

1H-imidazole-1-sulfonyl fluoride

7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50 - 70℃; for 8h; Reagent/catalyst; Temperature;80%
18156-74-6

1-(Trimethylsilyl)imidazole

A

1H-imidazole-1-sulfonyl fluoride

B

7189-69-7

N,N`-sulfuryldiimidazole

Conditions
ConditionsYield
With fluorosulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene under 0.750075 - 697.57 Torr; for 1.5h; Cooling;A 57%
B 33%
7189-69-7

N,N`-sulfuryldiimidazole

333-27-7

methyl trifluoromethanesulfonate

489471-57-0

3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.2h;100%
In dichloromethane at 0 - 20℃; for 3h;96%
In dichloromethane at 0℃; for 3h;94%
150-76-5

4-methoxy-phenol

7189-69-7

N,N`-sulfuryldiimidazole

1139705-25-1

4-methoxyphenyl 1H-imidazole-1-sulfonate

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran100%
With caesium carbonate In tetrahydrofuran at 20℃; for 12h;98%
With caesium carbonate In tetrahydrofuran at 20℃;93%
With sodium carbonate In N,N-dimethyl-formamide at 130℃;90%
Inert atmosphere; Basic conditions;

C24H32O4

7189-69-7

N,N`-sulfuryldiimidazole

C27H34N2O6S

Conditions
ConditionsYield
Stage #1: C24H32O4 With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: N,N`-sulfuryldiimidazole In tetrahydrofuran at -10 - 23℃; for 12h;
100%
Stage #1: C24H32O4 With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: N,N`-sulfuryldiimidazole In tetrahydrofuran at 23℃; for 12h; Inert atmosphere;
100%
Stage #1: C24H32O4 With lithium hexamethyldisilazane In tetrahydrofuran at 0℃;
Stage #2: N,N`-sulfuryldiimidazole In tetrahydrofuran at -10 - 20℃;
540-38-5

4-Iodophenol

7189-69-7

N,N`-sulfuryldiimidazole

C9H7IN2O3S

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran100%

1,1'-Sulfonyldiimidazole Specification

The CAS registry number of 1,1'-Sulfonyldiimidazole is 7189-69-7. The IUPAC name is 1,1'-sulfonylbis(1H-imidazole). Its EINECS registry number is 230-554-0. In addition, the formula is C6H6N4O2 and the molecular weight is 198.20244. What's more, it belongs to the classes of Imidazoles; Building Blocks; Heterocyclic Building Blocks. What's more, it is a kind of light cream crystalline powder.

Physical properties about this chemical are: (1)ACD/LogP: -0.86; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.86; (4)ACD/LogD (pH 7.4): -0.86; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 8.12; (8)ACD/KOC (pH 7.4): 8.12; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 78.16 Å2; (13)Index of Refraction: 1.722; (14)Molar Refractivity: 48.86 cm3; (15)Molar Volume: 123.4 cm3; (16)Polarizability: 19.37 ×10-24cm3; (17)Surface Tension: 76.7 dyne/cm; (18)Density: 1.6 g/cm3; (19)Flash Point: 238.7 °C; (20)Enthalpy of Vaporization: 73.37 kJ/mol; (21)Boiling Point: 471 °C at 760 mmHg; (22)Vapour Pressure: 4.82E-09 mmHg at 25°C.

Preparation 1,1'-Sulfonyldiimidazole: it can be prepared by 1-trimethylsilanyl-1H-imidazole. This reaction will need reagent SO2Cl2 and solvent toluene. The reaction time is 4 hours at temperature of -10 °C. The yield is about 98%.

1,1'-Sulfonyldiimidazole can be prepared by 1-trimethylsilanyl-1H-imidazole.

Uses of 1,1'-Sulfonyldiimidazole: it can react with 2-(4-chlorophenyl)-1-(4-methoxyphenyl)ethanol to get 1-[2-(4-chloro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-1H-imidazole. This reaction will need reagent acetonitrile. The reaction time is 2 hours with ambient temperature and the yield is about 61.6%.

1,1'-Sulfonyldiimidazole can react with 2-(4-chlorophenyl)-1-(4-methoxyphenyl)ethanol to get 1-[2-(4-chloro-phenyl)-1-(4-methoxy-phenyl)-ethyl]-1H-imidazole

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin and harmful by inhalation, in contact with skin and if swallowed. You should wear suitable protective clothing, gloves and eye/face protection when you are using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(n1ccnc1)n2ccnc2
(2)InChI: InChI=1/C6H6N4O2S/c11-13(12,9-3-1-7-5-9)10-4-2-8-6-10/h1-6H
(3)InChIKey: ZLKNPIVTWNMMMH-UHFFFAOYAJ

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